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Chapter 18: Q12P (page 581)

Predict the major product of each of the following reactions:

Short Answer

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Answer

Step by step solution

01

Step-by-Step SolutionStep 1: Reaction of epoxides (Ring-opening)

The epoxide ring is opened by a reaction with acid (HX) in ether, and the substitution pattern of the carbons in the epoxide ring tells where the ring-opening reaction occurs. The more hindered carbon (tertiary) is attacked from the backside, and cleavage occurs.

02

The major product of the reaction in (a)

  1. The ring-opening reaction in acid-catalyzed occurs at that carbon which is more hindered if one of the epoxide carbons is tertiary. In this reaction, the marked carbon is tertiary because two methyl groups are attached. The major product formed is,

Ring-opening reaction

03

The major product of the reaction in (b)

b. In this reaction, the tertiary carbon of the epoxide ring is marked by the arrow. The ring-opening reaction takes place, and the major product formed is shown below,


Ring-opening reaction

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Most popular questions from this chapter

Fluoxetine, a heavily prescribed antidepressant marketed under the

name Prozac, can be prepared by a route that begins with the reactionbetween a phenol and an alkyl chloride.

  1. The rate of the reaction depends on both phenol and alkyl halide. Is this an SN1 or an SN2 reaction? Show the mechanism.
  2. The physiologically active enantiomer of fluoxetine has (S) stereochemistry. Based on your answer in part (a), draw the structureof the alkyl chloride, you would need, showing the correct stereochemistry.

Predict the product(s) and provide the mechanism for each reaction below. What do the mechanisms have in common?

a.

b.

c.

d.

Acid-catalyzed hydrolysis of a 1,2-epoxycyclohexane produces a transdiaxial 1,2-diol. What product would you expect to obtain from acidic hydrolysis of cis-3-tert-butyl-1,2-epoxycyclohexane? (Recall that the bulky tert-butyl group locks the cyclohexane ring into a specific conformation.)

Anethole, \({C_{10}}{H_{12}}O\), a major constituent of the oil of anise, has the \({}^1H\) NMR spectrum shown. On oxidation with \(N{a_2}C{r_2}{O_7}\), anethole yields p-methoxybenzoic acid. What is the structure of anethole? Assign all peaks in the NMR spectrum, and account for the observed splitting patterns.

Show the structure and stereochemistry of the alcohol that would result if 1,2-epoxycyclohexane were reduced with lithium aluminium deuteride, LiAlD4?
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